Cheapest return flights from Chicago to San Juan in December from 237€

AirHint found the following cheapest return flights from Chicago (MDW) to San Juan (SJU) in December 2025 (see full year).

Return flights

05 Dec - 08 Dec Frontier Airlines
04 Dec - 09 Dec Frontier Airlines
03 Dec - 10 Dec Southwest Airlines
06 Dec - 10 Dec Southwest Airlines
30 Dec - 06 Jan Southwest Airlines
19 Dec - 28 Dec Southwest Airlines
26 Dec - 31 Dec Southwest Airlines
26 Dec - 03 Jan Southwest Airlines
26 Dec - 02 Jan Southwest Airlines
26 Dec - 04 Jan Southwest Airlines

Also check the deals for one-way flights from Chicago to San Juan in December.

Skyscanner

The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

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